Hydrochloric Acid → HCID 9905248, compound

HRID 443052Notes

Reaction equation

HRID 443052 reaction equation
[NH2:1][OH:2].C[O-].[Na+].[C:6]([C:8]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16]CC)=O)#[N:7].Cl>CO>[C:6]([C:8]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([NH:1][OH:2])=[O:16])#[N:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 10942334Sodium MethoxideHCID 54338793HCID 54338793, compound

Product 1

HCID 9905248HCID 9905248, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

To a solution of hydroxylamine (38.5 g, 0.55 mol) in methanol (300 ml) was added a solution of 28% sodium methylate in methanol (165 ml, 0.83 mol). To the mixture was added, while stirring under ice-cooling, a solution of ethyl 7-cyano-7,7-diphenylheptanoate (18.7 g, 0.055 mol) in methanol (50 ml). The mixture was stirred for 1.5 hour. After completion of the reaction, pH of the reaction mixture was made acidic with 1N HCl. The reaction mixture was subjected to extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous saline solution, followed by drying over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was crystallized from ethyl acetate--hexane to give 15.2 g of the title compound.

Workup

  1. additionTo the mixture was added
  2. temperaturecooling
  3. stirringThe mixture was stirred for 1.5 hour
  4. customAfter completion of the reaction, pH of the reaction mixture
  5. extractionThe reaction mixture was subjected to extraction with ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materialby drying over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customthe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-e19c273b8a524d7ab27b14054ff0b58d
Source dataset
uspto-grants-1999_04
Patent number
US05891916

Reaction notes

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